Simulated moving columns technique for enantioselective supercritical fluid chromatography.

Abstract:

:This article describes a very useful extension of an unique column switching technique called "Simulated Moving Columns" (SMC) that was previously reported for chiral high performance liquid chromatography (HPLC) (Zhang and McConnell, Journal of Chromatography A 2004;1028:227-238). SMC uses two or three short chiral columns connected in series, and enables the unresolved enantiomers to separate repeatedly and exclusively through each of the columns until sufficient resolution is attained. The technique is significantly enhanced through the use of supercritical fluid chromatography (SFC). The supercritical or near critical carbon dioxide (CO(2)) used in the mobile phase of SFC possesses the properties of a liquid as well as a gas, and usually results in much sharper peaks compared to HPLC. Consequently, by combining SMC with SFC (SMC-SFC), we were able to dramatically increase the number of SMC cycles with significantly less band broadening compared to HPLC. For the first time, an enantioselective SFC separation was demonstrated by increasing the column from the actual 20 cm length to reach a half meter virtual length with remarkably enhanced efficiency. Off-column band broadening resulting from a two-column SMC system was measured, and its impact on the enantioselectivity of SMC-SFC was found to be much less than in SMC-HPLC.

journal_name

Chirality

journal_title

Chirality

authors

Zhang Y,Dai J,Wang-Iverson DB,Tymiak AA

doi

10.1002/chir.20409

subject

Has Abstract

pub_date

2007-09-01 00:00:00

pages

683-92

issue

9

eissn

0899-0042

issn

1520-636X

journal_volume

19

pub_type

杂志文章
  • From cosmic chirality to protein structure: Lord Kelvin's legacy.

    abstract::A selection of my work on chirality is sketched in two distinct parts of this lecture. Symmetry and Chirality explains how the discrete symmetries of parity P, time reversal T, and charge conjugation C may be used to characterize the properties of chiral systems. The concepts of true chirality (time-invariant enantiom...

    journal_title:Chirality

    pub_type: 杂志文章,评审

    doi:10.1002/chir.22017

    authors: Barron LD

    更新日期:2012-11-01 00:00:00

  • Enhanced efficiency due to the use of achiral additives in the optical resolution of 1-phenylethylamine by its glutaric acid derivative.

    abstract::Racemic 1-phenylethylamine was optically resolved by its own derivative formed with glutaric acid namely (+)-(R)-N-(1-phenylethyl)glutaramic acid. The amide acid resolving agent was synthesized from (+)-(R)-1-phenylethylamine by N-derivatization. The glutaric acid derivative was the next in a homologous series of dica...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20377

    authors: Schindler J,Egressy M,Bereczki L,Pokol G,Fogassy E,Marthi K

    更新日期:2007-03-01 00:00:00

  • Enantiomer self-disproportionation and chiral stationary phase based selective chiral separation of organic compounds.

    abstract::In modern chromatography, chiral stationary phase (CSP) and enantiomer self-disproportionation (ESD) are new inventions of packing material offer a guarantee for a successful enantiomeric separation. All CSPs were synthesized by chemical bonding of the relevant organic moieties onto a porous parent silica material for...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20917

    authors: Mayani VJ,Abdi SH,Mayani SV,Kim HC,Park SK

    更新日期:2011-04-01 00:00:00

  • Chirality as an inherent general property of matter.

    abstract::A statement has been formulated that chirality is an indispensable inherent property of all material objects, at one level of organization of matter or another. The translation of chirality from one level of material objects to another deserves our attention. The parity violation of weak interactions can be discussed ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20271

    authors: Davankov V

    更新日期:2006-08-01 00:00:00

  • A systematic study of chiral homoprolinols and their derivatives in the catalysis of enantioselective addition of diethylzinc to aldehydes.

    abstract::Homoprolinol analogs, a class of optically active γ-amino alcohols, were examined systematically in the enantioselective addition reactions of diethylzinc to aldehydes. By comparison of the results catalyzed by these γ-amino alcohols with those by the β-amino alcohols based on pyrrolidine architecture reported in the ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.21017

    authors: Liu CL,Wei CY,Wang SW,Peng YG

    更新日期:2011-11-01 00:00:00

  • Excavations in drug chirality: 1. Cyclothiazide.

    abstract::There is a great deal of current interest in the role and importance of chirality in the development of new drugs, but little attention is being paid to the stereochemistry of older drugs. Indeed, many older chiral drugs were introduced without adequate information on their stereochemical identity or composition. We h...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530030103

    authors: Nusser E,Banerjee A,Gal J

    更新日期:1991-01-01 00:00:00

  • Absolute configuration determination of chiral molecules in the solution state using vibrational circular dichroism.

    abstract::Advances in the measurement, calculation, and application of vibrational circular dichroism (VCD) for the determination of absolute configuration are described. The purpose of the review is to provide an up-to-date perspective on the capability of VCD to solve problems of absolute stereochemistry for chiral molecules ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10287

    authors: Freedman TB,Cao X,Dukor RK,Nafie LA

    更新日期:2003-11-01 00:00:00

  • Isolation and identification of sapotexanthin 5,6-epoxide and 5,8-epoxide from red mamey (Pouteria sapota).

    abstract::Two new carotenoids, sapotexanthin 5,6-epoxide and sapotexanthin 5,8-epoxide, have been isolated from the ripe fruits of red mamey (Pouteria sapota). Sapotexanthin 5,6-epoxide was also prepared by partial synthesis via epoxidation of sapotexanthin, and the (5R,6S) and (5S,6R) stereoisomers were identified by high-perf...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23206

    authors: Murillo E,Agócs A,Nagy V,Király SB,Kurtán T,Toribio EM,Lakey-Beitia J,Deli J

    更新日期:2020-05-01 00:00:00

  • Enantioselective synthesis of 2- and 3-substituted 2,3-dihydro[1,4]dioxino[2,3-b]pyridine derivatives and enantiomeric purity control by capillary electrophoresis.

    abstract::A rapid and simple procedure for enantioselective preparation of 2- and 3-substituted 2,3-dihydro[1,4]dioxino[2,3-b]pyridine derivatives (A and B, respectively) is described. The enantiomeric purity of each isomer was determined by capillary electrophoresis using a dual-cyclodextrin system (S-beta-CD/beta-CD) dissolve...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20090

    authors: Lazar S,Soukri M,El Haddad M,Akssira M,Leger JM,Jarry C,Morin P,Guillaumet G

    更新日期:2005-01-01 00:00:00

  • Enantioselectivity in the steady-state pharmacokinetics and transplacental distribution of pindolol at delivery in pregnancy-induced hypertension.

    abstract::Nine patients taking oral doses of 10 mg/12 h rac-pindolol as part of their treatment for hypertension in pregnancy were recruited for the study. Maternal and fetal gestational age ranged from 20-38 years and 28-41 weeks, respectively. Blood was collected from the umbilical cord vein and from the mother from zero to 1...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10124

    authors: Gonçalves PV,Matthes Ado C,Da Cunha SP,Lanchote VL

    更新日期:2002-08-01 00:00:00

  • N,N-dimethylcarbamyl derivatives of oxazepam.

    abstract::Three N,N-dimethylcarbamyl derivatives of oxazepam (1-(N,N-dimethylcarbamyl)oxazepam, 3-O-(N,N-dimethylcarbamyl)oxazepam, and 1,3-O-bis(N,N-dimethylcarbamyl) oxazepam) and a 3-O-acyl-1-(N,N-dimethylcarbamyl)-oxazepam were synthesized from either oxazepam or demoxepam. Enantiomeric pairs of these derivatives and of cam...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530030313

    authors: Yang SK,Lu XL

    更新日期:1991-01-01 00:00:00

  • Additional criterion for the determination of the handedness of 2(1) helices in crystals of bile acids: Crystal structure of a tert-butylphenyl derivative of cholic acid.

    abstract::[3β,5β,7α,12α]-3-(4-t-Butylbenzoilamine)-7,12-dihydroxycholan-24-oic acid was synthesized and recrystallized from chlorobenzene and acetone. Orthorhombic P2(1)2(1)2(1) and monoclinic P2(1) crystals were obtained, respectively, and both crystals include solvent and water molecules with a 1:1:1 stoichiometry. In the sec...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.21020

    authors: Meijide F,Trillo JV,Soto VH,Jover A,Tato JV

    更新日期:2011-11-01 00:00:00

  • Solid-state circular dichroism and hydrogen bonding, part 2: the case of hypothemycin re-investigated.

    abstract::The impact of crystalline forces on the solid-state circular dichroism (CD) spectrum of hypothemycin (), a biologically active molecule extracted from natural sources, has been analyzed by means of time-dependent density functional theory CD calculations. Input structures were extracted from the X-ray geometry of and ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22008

    authors: Pescitelli G

    更新日期:2012-09-01 00:00:00

  • Effect of serum lipoproteins on stereoselective halofantrine metabolism by rat hepatocytes.

    abstract::Experimental hyperlipidemia has shown to decrease cytochrome P450 3A4 and 2C11 expression and to increase liver concentrations and the plasma protein binding of halofantrine (HF) enantiomers. The present study examined the effect of hyperlipidemic (HL) serum on the metabolism of HF enantiomers by primary rat hepatocyt...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22054

    authors: Patel JP,Hamdy DA,El-Kadi AO,Brocks DR

    更新日期:2012-07-01 00:00:00

  • Molecular enantiorecognition of l-glucose and d-glucose in whole blood samples.

    abstract::In the past years, enantioanalysis became very important for clinical analysis; biomarkers/substances of biomedical importance with chiral structure should be analyzed and their presence correlated with the specific disorder. Therefore, we developed a method for the assay of l- and d-glucose, based on molecular recogn...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22843

    authors: Stefan-van Staden RI,Mitrofan G

    更新日期:2018-05-01 00:00:00

  • Unusual temperature-induced retention behavior of constrained β-amino acid enantiomers on the zwitterionic chiral stationary phases ZWIX(+) and ZWIX(-).

    abstract::The effects of temperature on the chiral recognition of cyclic β-amino acid enantiomers on zwitterionic [Chiralpak ZWIX(+) and ZWIX(-)] chiral stationary phases were investigated. Experiments were performed at different mobile phase compositions and under 10°C column temperature increments in the temperature range 10-...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22333

    authors: Ilisz I,Pataj Z,Gecse Z,Szakonyi Z,Fülöp F,Lindner W,Péter A

    更新日期:2014-08-01 00:00:00

  • Pharmacokinetics of nateglinide enantiomers and their metabolites in Goto-Kakizaki rats, a model for type 2 diabetes mellitus.

    abstract::The pharmacokinetics of (-)-N-(trans-4-isopropylcyclohexanecarbonyl)-D-phenylalanine (nateglinide) and its enantiomer (L-enantiomer) was studied in Goto-Kakizaki (GK) rats after intravenous administration of nateglinide or L-enantiomer at a dose of 40 micromol/kg body weight. Nateglinide, its L-enantiomer and their me...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20711

    authors: Tamura M,Shiba S,Kudo N,Kawashima Y

    更新日期:2010-01-01 00:00:00

  • Alpha-aminophosphonates as novel organocatalysts for asymmetric Michael addition of carbonyl compounds to nitroolefins.

    abstract::A cyclic alpha-aminophosphonate was found to be a novel organocatalyst for Michael type addition reactions of carbonyl compounds to nitroolefins to afford the corresponding adducts in high enantio- and diastereoselectivities. ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20552

    authors: Tao Q,Tang G,Lin K,Zhao YF

    更新日期:2008-07-01 00:00:00

  • A stereodynamic fluorescent probe for amino acids. Circular dichroism and circularly polarized luminescence analysis.

    abstract::The use of stereodynamic probes is becoming one of the leading strategies for the fast and effective determination of enantiomeric excess. Recently, we reported a series of novel molecular architectures based on a modified tris(2-pyridylmethyl)amine complex (TPMA), which are able to amplify the electronic CD, in the c...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22780

    authors: Carmo Dos Santos NA,Badetti E,Licini G,Abbate S,Longhi G,Zonta C

    更新日期:2018-01-01 00:00:00

  • Highly enantioselective HPLC separations using the covalently bonded macrocyclic antibiotic, ristocetin A, chiral stationary phase.

    abstract::The macrocyclic glycopeptide, ristocetin A, was covalently bonded to a silica gel support and evaluated as a liquid chromatographic (LC) chiral stationary phase (CSP). Over 230 racemates were resolved in either the reversed-phase mode, the normal-phase mode, or the polar-organic mode. The retention behavior and select...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(1998)10:5<434::AID-CHIR10>

    authors: Ekborg-Ott KH,Liu Y,Armstrong DW

    更新日期:1998-01-01 00:00:00

  • High-performance liquid chromatographic resolution of oxamniquine enantiomers: application to in vitro metabolism studies.

    abstract::A method is described for the HPLC analysis of oxamniquine enantiomers in liver fraction incubates, using a second-generation alpha 1-acid glycoprotein-based column (Chiral-AGP). Oxamniquine is extracted from the incubation media by liquid-liquid extraction, using diethyl ether. The dried residue is redissolved in elu...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530020413

    authors: Noctor TA,Fell AF,Kaye B

    更新日期:1990-01-01 00:00:00

  • Synthesis of novel camphor-derived bifunctional thiourea organocatalysts.

    abstract::Synthesis and catalyst performance of 2,3- (types and ) and 2,8-disubstituted (type ) thiourea bifunctional organocatalysts was attempted. The synthesis of catalyst of type has, so far, not been realized, while catalysts of type , i.e., the 2,3-exo- and the 2-endo-3-exo-thiourea catalysts, were prepared in six steps s...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22386

    authors: Ričko S,Golobič A,Svete J,Stanovnik B,Grošelj U

    更新日期:2015-01-01 00:00:00

  • Synthesis of epimers of L-cyclopentenylglycine using enzymatic resolution.

    abstract::Both epimers of the naturally occurring nonproteinogenic amino acid L-cyclopentenylglycine, (2S,1'S)- and (2S, 1'R)-2-(cyclopent-2'-enyl)glycine, were obtained via a procedure involving condensation of 3-chlorocyclopentene with diethyl acetylaminomalonate, deethoxycarbonylation, chromatographic separation of the resul...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/1520-636X(2000)12:9<665::AID-CHIR4>3.0.CO;

    authors: Andersen L,Nielsen B,Jaroszewski JW

    更新日期:2000-10-01 00:00:00

  • Improvement of enantioselective syntheses and chiral high resolution gas chromatographic analyses of (+)-2-allyl-2-carboethoxy-cyclopentanol.

    abstract::The improvement of the biocatalytic reduction of 2-allyl-carboethoxy-cyclopentanone (2) to the corresponding cyclopentanol derivative (+)-(1R,2R)-(1) was accomplished employing baker's yeast in organic media. This chiral cyclopentanol derivative (1), analyzed by high resolution gas chromatography performed over beta-c...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(1997)9:4<321::AID-CHIR1>3.

    authors: Fraga CA,Barreiro EJ,da Silva EF,dos Santos AR,KV Ramos MdaC,de Aquino Neto FR

    更新日期:1997-01-01 00:00:00

  • Enantioseparation of chiral perfluorooctane sulfonate (PFOS) by supercritical fluid chromatography (SFC): Effects of the chromatographic conditions and separation mechanism.

    abstract::Perfluorooctane sulfonate (PFOS) is one of the most frequently detected perfluoroalkyl substances in environmental and human samples. Previous studies have shown that nonracemic PFOS in biological samples can be used as a marker of PFOS exposure sources. In recent years, supercritical fluid chromatography (SFC) has em...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23120

    authors: Zhao L,Chen F,Guo F,Liu W,Liu K

    更新日期:2019-10-01 00:00:00

  • Asymmetric allylation of α-ketoester-derived N-benzoylhydrazones promoted by chiral sulfoxides/N-oxides Lewis bases: highly enantioselective synthesis of quaternary α-substituted α-allyl-α-amino acids.

    abstract::Chiral sulfoxides/N-oxides (R)-1 and (R,R)-2 are effective chiral promoters in the enantioselective allylation of α-keto ester N-benzoylhydrazone derivatives 3a-g to generate the corresponding N-benzoylhydrazine derivatives 4a-g, with enantiomeric excesses as high as 98%. Representative hydrazine derivatives 4a-b were...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22159

    authors: Reyes-Rangel G,Bandala Y,García-Flores F,Juaristi E

    更新日期:2013-09-01 00:00:00

  • Theoretical Modeling of Surface Confined Chiral Nanoporous Networks: Cruciform Molecules as Versatile Building Blocks.

    abstract::Patterning of solid surfaces with functional organic molecules has been a convenient route to fabricate two-dimensional materials with programmed architecture and activities. One example is the chiral nanoporous networks that can be created via controlled self-assembly of star-shaped molecules under 2D confinement. In...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22437

    authors: Kasperski A,Szabelski P

    更新日期:2015-07-01 00:00:00

  • Absolute stereochemistry of unusual biopolymers from Ascomycete culture LL-W1278: examples that derivatives of (S)-6-hydroxymellein are also natural fungal metabolites.

    abstract::The new linear polyesters, W1278-A, B, and C, were isolated from culture extracts of a freshwater Ascomycete fungus. Their structures were elucidated on the basis of spectroscopic analyses and chemical transformations, with the absolute configuration established by the circular dichroism (CD) method using (R)-(-)-6-hy...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20105

    authors: Schlingmann G,Roll DM

    更新日期:2005-01-01 00:00:00

  • Demonstration of spontaneous chiral symmetry breaking in asymmetric Mannich and Aldol reactions.

    abstract::Spontaneous symmetry breaking in reactive systems, known as a rare physical phenomenon and for the Soai autocatalytic irreversible reaction, might in principle also occur in other, more common asymmetric reactions when the chiral product is capable to promote its formation and an element of "nonlinearity" is involved ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20474

    authors: Mauksch M,Tsogoeva SB,Wei S,Martynova IM

    更新日期:2007-11-01 00:00:00

  • Enantioselective separation of (±)-β-hydroxy-1,2,3-triazoles by supercritical fluid chromatography and high-performance liquid chromatography.

    abstract::This paper reports the enantioseparation of β-hydroxy-1,2,3-triazole derivatives, which present a broad range of biological properties, by supercritical fluid chromatography (SFC) and high-performance liquid chromatography techniques (HPLC). Polysaccharide-based chiral columns (cellulose and amylose) were used to eval...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22851

    authors: Alvarenga N,Porto ALM,Barreiro JC

    更新日期:2018-07-01 00:00:00